My name is Tiffany – Pt. 1 [bi][t/mmm][Crossdressing][Gangbang]

*This is part of the “My name is Tiffany” Series.*

*Adventure Number 1 – The Basketball Gangbang (Part 1 of 2)*

**Chapter 1**

Hi. My name is Tiffany.

Well, it wasn’t always Tiffany. I used to be a boy, but that was a long time ago.
Now i’m a pretty girl, and my life is so much better than I used to be. At my new school, I have friends, and i finally made cheer squad. Things were different before. I had a date tonight, and I was excited.

I met Darrell the first time I went jogging as a girl. I had been dressing for some time – I had gotten better at putting on my makeup, and all the squats I was doing were finally giving me the cute butt I had always wanted, But this was the first time I had exercised in public, as a girl. I was too nervous to go to the gym at first, I thought this would be less scary.

I had spent days picking out the perfect outfit. My job at the coffee shop didnt leave me with a lot of extra cash, but my boss was a handsome and kind older man, who allowed me to dress at work and made sure nobody harassed me. I spent the whole weekend shopping online, and pieced together the cutest workout gear.

I had bright pink boyshorts on, the hips and butt were a pretty lace pattern but the front was silky smooth and had a black star in the middle. They felt amazing on my creamy white skin. I found a pink sports bra that matched it, and it held my breast forms so well that you couldn’t tell they were fake.

Over these I wore a pink and black skirt, you know the kind with the criss cross schoolgirl pattern? I had black Nike`s with a pink stripe, and a black crop top. My fake lashes were on, and the teal eyeshadow complimented my pink lips. The long blonde wig I picked out from the mall was done up in a ponytail, with a fluffy pink scrunchy for bonus points.

Nervously, I stepped out onto the front porch, pulling the door closed behind me. I took a deep breath, smiled, and skipped down to the sidewalk. The sun was out, there were a few clouds, and the flowers were in bloom. It was a beautiful July day, and I was going to enjoy it.

As I picked up the pace, I pondered just how quiet my neighborhood was in the afternoon. I could probably do this more often… Everyone was still at work. The only people who were home were the new college guys that had just moved in at the end of the block. I was sure I could get a few laps in without bumping into anyone – I just had to be careful passing their house.

When I heard them it was already too late. I passed the tall green hedge obscuring my view of their driveway, and there they were. The 3 of them were playing basketball, sweat pouring down their faces, their strong legs showing under this baggy shorts. There was something else under those shorts too..

**Chapter 2**

They all turned when I came past the hedge and I knew I was caught.

I hadn’t met them as a boy yet, so if I played it cool and then went on my way, they might never connect the dots..

“Hey sweetie, where you goin` in such a hurry?”
It was the tall one. His dark skin framed his gorgeous eyes so well.
“My name is Tiffany” I squeaked, doing my best girl voice. I wanted to practice more, but my roommate was home all the time and it was hard to not get caught. I gave him a little smile, and tilted my head to the side a bit.

“What’s yours?”
“Im Darrell. This is Rich, and Mike.” He pointed to his friends.
“It’s nice to meet you all, but Im in a bit of a hur-”
He cut me off, “Then slow down hun.”

He put his hand around my shoulder gently as I tried to walk past him, slowly turning me around to face his friends. His arm was heavy, his hands so big, and the weight of it on me was comforting. I felt safe, and fragile, yet protected. I liked it.

“Come on inside, weve got some lemonade.” His buddys laughed.
I wanted to say no, but I had butterflies in my tummy and just stammered.
Oh god, what if they found out I was a boy? Would they hurt me?

They brought me inside and we all sat on the couch. Before I could say anything,
Darrell leaned in and started kissing me. He pinned one hand on each side of my head, and his warm body pressed down on mine. Mike and Rich were on either side of me, and I felt their hands start caressing my legs.

They were getting so close. I fought with all my strength to keep my clitty soft, but I was in heaven and I just could not help myself. I felt my skirt begin to rise and I panicked.

“Darrell, what the fuck!” It was Mike, as his hand jerked back. Darrell stopped and looked down, then gave me a smile. His teeth were white and straight, his lips maroon. His right hand moved from my wrist to my throat, and he squeezed ever so gently.

“You some kind of sissy boy Tiffany? Do you get off on this?”
“Yes Da-” He was not choking me, but I was short of breath and nervous.
“Not Darrell. Daddy.”
“Yes, Daddy” I whimpered.

**Chapter 3**

“What are you doing man?” It was Rich this time.
“He clearly wants to get fucked,” Darrell said, “I think we should him him. Let’s teach this sissy a lesson. Help him decide if really wants to be girl – If he can handle being a girl.”
Mike glanced at Rich. I couldn’t tell if it was confusion, excitement, or both.

“Plus,” Darrell continued, “Tiffany`s not going to tell anybody, are you?”
I bit my lip and nodded, looking up at him with my blue eyes wide, false eyelashes flapping.
Darrell started kissing me again. Rich began slipping my skirt down my legs, and Mike was squeezing my butt, his fingers moving slowly inward, flirting with my smooth, warm boy pussy. My heart was racing, My breath was short, my mind was blank. I felt warm and fuzzy all over. Oh god, this was happening!

Darrell pulled down his shorts and I gasped. His cock was enormous. I had heard the jokes, stories from my girl friends, but never had seen something so beautiful. It was thick, and looked like it was soft, but would feel firm in my hands. I licked my lips. I had always wondered what a real piece of meat would taste like. “Please.”, I said to Darrell softly, and he knew what I wanted.

He placed his hand on my cheek, spreading my lips with his thumb, and pressed the head of his shaft on my tongue. It was so thick, I could barely get my lips around it. It was slippery with sweat, felt soft and warm, and tasted better than any pussy I had ever eaten.

“Mmmph..” I moaned a little as I looked up at him, placing my hands on his thighs as he stood over me on the couch. Rich had slipped my clitty out from under my boyshorts, and wrapped his first two fingers around it – even when I was hard, it was still very small, but the pleasure I felt from his strong, soft, dark hands was so large.

I began to bob my head back and forth, slipping Darrell`s cock as deep as i could into my mouth, my pink lips stretched to their most and wrapping around him, as his sweat mixed with slobber and I felt myself slip away. I wrapped first one hand around his shaft, then two, and I pumped as I licked and sucked, and I completely lost control. I felt like a starved prisoner at her first drink of water, desperate and ravenous for more.

Mikes fingers were inside me know, and I was squirming. My hips were rocking back and forth, pressing my boy pussy down on his thick fingers, feeling Richs strokes as I rode them back up. Darrell had one hand underneath my chin, and the other wrapped around my ponytail, careful not to mess my wig up. I`d never felt so aroused in my life.

And then he came. I was so delicious. It was warm, and sweet, like a sticky syrup or nectar, and a little salty after like caramel. As he pumped my mouth full of himself, he moaned loudly and I felt his thighs shake. His large, smooth sack bounced, contracting slightly with each burst. I smiled at him, lips covered with cum, and mumbled a soft “Thank you” before swallowing.

Source: reddit.com/r/sexystories/comments/7uhtw8/my_name_is_tiffany_pt_1